This monstrosity of a trip was actually the result of combining three different vacations. I’ll split the planning out into three sections, outlying how I went about booking each portion, and the confluence of events that led to linking these trips together to create a 15-day, multi-continent adventure!

The original trip: Denver to Tokyo on the 787 Dreamliner

In May 2012, on the day that United announced their first official international 787 Dreamliner route from Denver to Tokyo-Narita, they uploaded it into the schedule with an abnormallylow price of ~$900 round-trip on their B-fare. A United B-fare is a full-fare economy ticket, which would normally cost several thousands of dollars. This sort of fare earns 1.5X Premier Qualifying Miles, which help one build United status. Additionally, this fare was available for what was supposed to be the inaugural flight for this route, and the inaugural international 787 flight for United. Several friends on Milepoint booked this same flight, so it was to be a “party-flight.” A sub-$1,000 fare to Tokyo is pretty good in general, but the fact that this was a B-fare, and that this was supposed to be the inaugural flight made it a must-have.

Denver to Tokyo-Narita

I originally planned this trip to be March 31 through April 6, and planned to spend the week in Japan. As it turns out, the 787 had its share of problems after its initial release, and was subsequently grounded in January. By the end of February, United finally made the official announcement that the inaugural would be postponed to a later date, so this inaugural was no longer a possibility. I was left contemplating when I wanted to change this flight to…

Another unrelated trip: TAM airfare deal from New York to Santiago

In November 2012, an extremely low round-trip fare of ~$330 appeared for flights from New York or Miami to both Buenos Aires and Santiago on TAM Airlines (of Brazil) through Orbitz. After a late-night call from a friend, I decided to book a couple of these flights – a trip to Buenos Aires in March 2013 and one to Santiago in June.

I ended up selecting a routing from New York-JFK to Santiago. After a litany of schedule changes by TAM, and after dealing with a series of hour-long phone calls to Orbitz, I ultimately ended up with a trip from New York to Santiago, via Rio de Janeiro on the outbound and via Sao Paulo on the return.

New York-JFK to Santiago (SCL) via Rio de Janeiro (GIG) on outbound and Sao Paulo (GRU) on the return

Joining the gang in Dubai

As I pondered when I should take my DEN-NRT flight on the 787, I decided that I wanted to spend some time in Japan, but at the same time try to somehow get over to Dubai to meet a group of ten friends who would be there, and to see my old roommate who moved to Dubai last year. They would all be in Dubai during the heat of the summer, from June 20th-23rd. I checked award availability and found an absolute gem on the American Airlines award flight

American OneWorld Award Chart from AA.com

This particular award allows for a trip from Asia Zone 1 (Japan, etc) to India and the Middle East for only 22.5k miles each way in economy, 30k AA miles each way in business class, or 45k in First. Compare that to the Star Alliance options of United (45k/67.5k/87.5k) and US Airways (40k/60k/90k), as well as Delta (40k/60k), and you can see that this is an absolute steal!

Tokyo to Dubai Award Comparison

Luckily, I had a decent sized stash of American AAdvantage miles stored up after a couple of credit card signing bonuses and a few flights to Europe from a couple years back, so I decided to redeem an award in business class.

With this award in mind, I needed to find availability for one of American’s OneWorld partners on the route. I ‘ll make no bones about it – I wanted to try Cathay Pacific. Ideally, I would have flown in first class, but since Cathay operates its HKG-DXB route with a two-class A330-300 aircraft, this would not be possible. So instead, I settled on business class – a pretty sweet consolation price considering that this plane features arguably the best business class seat in the world.

Cathay Pacific’s new Business Class. Picture: Cathay Pacific

So I headed over to the Qantas website to check award availability for Tokyo to Dubai. I wanted to arrive on June 20th and depart the night of June 23rd. I was pleased to see that the exact flights I wanted were available, so I jotted down the flight numbers and called them into American. After a five minute phone call, I had secured a round-trip from Tokyo to Dubai via Hong Kong in Cathay Pacific business class for 60,000 AAdvantage miles and about $85 in taxes.

Tokyo to Dubai via Hong Kong

Sewing it all together

So, now I had the Dubai portion booked. Given that it was pretty close to the end of my previously planned Santiago trip, I decided to move the outbound DEN-NRT segment to arrive Tokyo the same day as my Cathay Pacific flight to Hong Kong and then Dubai. I did want to spend about three days in Tokyo, so I added on several days in Tokyo after Dubai, and scheduled a return from NRT-DEN for June 27th.

I was able to adjust the dates of my Santiago flight due to the multitude of schedule changes to mesh nicely with the rest of my trip. This left me getting into New York the morning of June 17th and a flight from Denver to Tokyo on June 18th. So I looked for a flight from New York to Denver on the 17th. I was able to find a very reasonable round-trip fare on United from NewYork-LaGuardia to Denver departing the late afternoon of the 17th and returning to Washington-Dulles the evening of June 27th. Perfect.

After finding a very cheap Delta flight from Washington-Reagan (DCA) to JFK on the date of my outbound flight to Santiago on June 13th, I was all set.

Domestic flights — the missing pieces to the puzzle

Adding to the sheer awesomeness of this trip, I was upgraded to United BusinessFirst on both the DEN-NRT and NRT-DEN flights on the 787! That will equate to almost 24 hours in a lie-flat business seat, thanks to using a friend’s United Global Premier Upgrade (GPU) and a Mileage Upgrade (30,000 miles).

My ride to Tokyo: The United 787 BusinessFirst cabin (from my first trip on the 787)

All this craziness resulted in a fifteen night trip, visiting five cities and three continents. The final product looks something like this:

June 13: Washington-Reagan (DCA) – New York (JFK) on a Delta CRJ-900 in economy comfort

June 13: JFK – Rio de Janeiro, Brazil (GIG) on a TAM A330-200 in economy

June 14: 9-hour layover in Rio!

June 14: GIG – Santiago, Chile (SCL) on a TAM A320 in economy

June 14-16: Two nights in Santiago at a hostel.

June 16: SCL-Sao Paulo (GRU) on a LAN B767-300 in economy

June 16: GRU – JFK on a TAM B777-300ER in economy

June 17: New York-LaGuardia (LGA) – Denver (DEN) on a United B757-200 in economy plus

June 17: Overnight in Denver at the Aloft Denver Airport

June 18: DEN – Tokyo-Narita (NRT) on a United B787-8 in BusinessFirst

June 19: NRT – Hong Kong (HKG) on a Cathay Pacific B777-300 in Business

June 20: HKG – Dubai (DXB) on a Cathay Pacific A330-300 in Business

June 20-23: Three nights in Dubai at the Park Hyatt, Dubai

June 23: DXB – HKG on a Cathay Pacific A330-300 in Business

June 24: HKG – Tokyo-Hanaeda (HND) on a Cathay Pacific B777-300ER in Business

June 24-27: Three nights in Tokyo at the Park Hyatt, Tokyo

June 27: NRT-DEN on a United B787-8 in BusinessFirst

June 27: DEN – Washington-Dulles on a United B757-200 in economy plus

Whew! That’s a lot of travel, but I actually enjoy flying on airplanes – especially in business class. In all, this trip will consist of five nights on airplanes and ten in hotels. It will cover 38,856 total miles. Since TAM is a member of Star Alliance (for now), this total trip will earn me 31,789 United Premier Qualifying Miles and about 36,761 United Redeemable miles from just the TAM and United segments.

Well, let’s start this thing! I’ll try to give some timely first impressions throughout the course of my trip, and will follow it up with a full-fledged trip report afterwards.

EDIT: Well, as it turns out, weather did not cooperate with me, so I’ve already deviated from the above plan by heading to NYC a night early. I’ll make a separate post on that whole fiasco later on.